The Future of Insurance Podcast – Matt Masiello


Season 3, Episode 8, July 26, 2022

Guest Bio

As CEO of SIAA, Matt Masiello has responsibility for executive management of the largest alliance of independent insurance agencies in the United States and its related companies, providing leadership to senior executives of SIAA and Master Agencies across the country.

His more than 28 years of experience at SIAA and SAN Group have instilled in him the skills, knowledge, and expertise to lead SIAA and SAN Group (SIAA’s original and largest Master Agency operating across the Northeast). Matt has responsibility for the overall success of both companies, as well as providing strategic vision and leadership for their futures.

SIAA has 48 master agencies covering all 50 states with 13% of all U.S. independent insurance agencies as members, which write over $10 billion in premium, making SIAA the largest national independent insurance agency partnering network.

Matt is also the author of the book, Insurance Agency 4.0, available now.

Highlights from the Show

  • Matt has been in the independent agent channel for nearly 30 years, for his entire career
  • SIAA started in 1995, and is a national alliance of independent agencies with 48 master agencies, and has three focus areas:
    • Market access, which has become table stakes today
    • Generating top line revenue for agencies beyond commission to help them thrive
    • Agency development services to help agencies when starting up, through to the most mature agencies
  • They also help carriers interact with and manage relationships with independent agents by providing scale and coordination to the carriers, as well
  • So much of the economy is concentrated in small businesses, and that’s true of agencies, too, where 70% of agencies are under $1.2m in revenue
  • With all the talk over the years of threats to the independent agent channel, Matt is extremely excited about the prospects for the channel today
  • Some of acquisition and consolidation at the upper end of the channel has helped to spark innovation and entrepreneurialism on the smaller end, including the starting up of new agencies
  • He’s lived through other threats that were supposed to end the channel, like banks moving into insurance in the 1990s or the internet in the early 2000s
  • Today, there’s a lot of talk about Embedded insurance, which is being talked about as putting agents out of business
    • Matt sees Embedded taking some sales
    • But he also sees a lot of situations where Embedded isn’t designed to respond, like people with more complex needs, multiple policies across lots of products (Home, multiple Autos, Umbrella, Life, etc)
  • Part of the way agents will survive is through being purposeful in the kind of customers they target, and ensuring they have the tools to serve those customers and offer them value
    • That goes for the value agents offer to carriers, as well, including market access but also providing the advice, guidance and other valuable services that carriers need agents to do
  • Some advise agents to pull back from spaces where direct or digital are too threatening, like personal auto, but Matt sees that being the wrong answer
    • We talked about how US car makers pulled back from selling sedans, but consumers still buy them from other manufacturers – the US car companies just weren’t making sedans people wanted to buy
    • People are still buying personal insurance and need protection, so just be sure your offering meets their needs
    • The key is not to go after the price-sensitive, monoline shopper, but look for the one who needs multiline protection and values advice, guidance and support
  • You have to know your segment, but then recognize that its changing and has evolving needs, so you must interact with it differently
    • The days of just quoting someone’s auto policy are gone as 70-80% of people are starting their insurance journey online, so an agent needs to be digital to interact with those people, and then take them on the rest of the journey for the broader insurance needs they have rather than just thinking about the single policy
  • SIAA acquired Ryan Hanley’s Rogue Risk, bringing Ryan into the fold
    • This is about having an incubation path for people who want more freedom but aren’t yet ready to own their own agency yet
    • It also gives SIAA a test bed or sandbox to try the new digital tools and processes or ways of working that could help the channel thrive
  • Some of the startup insurtech carriers/MGAs may or may not be solving an insurance problem, but they’ve created something within their transaction or experience capabilities that traditional carriers haven’t solved for, which is valuable for the industry
  • The core challenge of the industry is that we’re doing things based on the constraints of our processes, but the consumer doesn’t care
  • This isn’t just about the end consumer, but agents, too – carriers need to think about the cost of doing business with that carrier as agents will avoid carriers who make their lives harder or more onerous
  • Matt sees this as the greatest time to be an agent as he’s ever seen
    • It may look different from how it’s looked in the past, but that’s true of any period in time, and that’s ok – as long as you’re willing to embrace what’s changing
    • Now is the time to come out swinging, implementing digital capabilities and be on the offense in demonstrating the value your provide your customers and your community


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This episode is brought to you by Ascend ( and by The Future of Insurance thought leadership series ( from Bryan Falchuk.

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